Hydrochloric Acid → 2-Chloro-5-nitrobenzyl alcohol

HRID 2374224Notes

Reaction equation

HRID 2374224 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](O)=[O:5].ClC1C=CC([N+]([O-])=O)=CC=1C=O.[BH4-].[Na+].Cl>CO.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 172872-Chloro-5-nitrobenzoic acidHCID 729332-Chloro-5-nitrobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 5557222-Chloro-5-nitrobenzyl alcoholYield 96.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Preparation of 2-chloro-5-nitrobenzoyl alcohol 30 g of 2-chloro-5-nitrobenzaldehyde was dissolved in 500 mL of methanol and cooled to 0° C. A solution of 10 g of sodium borohydride in 100 mL of water was then added dropwise over 90 minutes while maintaining the temperature below 10° C. The resultant reaction mixture was then stirred for one hour, then acidified with 2N HCl and left stirring overnight. The solids were then, washed with water and dried, to produce 27 g of 2-chloro-5-nitrobenzyl alcohol as a white solid.

Workup

  1. temperaturewhile maintaining the temperature below 10° C
  2. customThe resultant reaction mixture
  3. waitleft
  4. stirringstirring overnight
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-29b4b97510874627961be0a5d1e611f7
Source dataset
uspto-grants-2008_12
Patent number
US07462608B2

Reaction notes

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